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0 °C

Methyl (4S)-3-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2-oxo-1,3-oxazolidine-4-carboxylate (0.20 g, 0.52 mmol), prepared in step 2 of Example 70, was dissolved in 5 mL of tetrahydrofuran and cooled to 0° C. Lithium borohydride (2M solution in tetrahydrofuran, 0.57 mL, 1.14 mmol) was added and the mixture was stirred for 2 h. The mixture was allowed to warm to 25° C. and stirred for an additional 30 min, quenched with H2O and then 2 mL of 2N HCl was added. The mixture was diluted with 10 mL of water and poured into ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined and washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (25% acetone/hexane) afforded the title compound (124 mg, 69%) as a white solid. mp 189-192° C. HRMS: calcd for C13H11BrN2O3S+H+, 354.97465; found (ESI, [M+H]+), 354.9742. Analytical HPLC: retention time 9.2 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

1. temperatureto warm to 25° C.
2. stirringstirred for an additional 30 min
3. customquenched with H2O
4. addition2 mL of 2N HCl was added
5. additionThe mixture was diluted with 10 mL of water
6. additionpoured into ethyl acetate
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with ethyl acetate
9. washwashed with water, brine
10. dry with materialdried over anhydrous MgSO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure